FluoroMethyl 2-pyridyl sulfone

Fluoromethyl 2-pyridyl sulfone and its derivatives can be used as novel monofluoromethylation reagents. The monofluorinated sulfinate intermediates during the monofluoroolefination of aldehydes and ketones can be halogenated in situ to afford mono- and dihalofluoroalkyl compounds. The coupling reaction between iodofluoromethyl 2-pyridyl sulfone and aryl iodides mediated by copper can be used to prepare monofluoromethyl arenes and heteroarenes.

white solid

(1) Dihalofluoromethylation of aldehydes and ketones.
(2) Halofluoroalkylation of aldehydes.

(3) Monofluoromethylation of arenes and heteroarenes.

[1] YANCHUAN ZHAO Jinbo H Bing Gao. From Olefination to Alkylation: In-Situ Halogenation of Julia–Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds[J]. Journal of the American Chemical Society, 2012, 134 13: 5790-5793. DOI:10.1021/ja301601b.
[2] YANCHUAN ZHAO. Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group[J]. Organic Letters, 2012, 14 23: 6080-6083. DOI:10.1021/ol3029737.